Doug Ashley

Chestertown MD

Doug Ashley Realtors, LLC

57 Closed Sales

$22.2M Total Value

$50K - $4.3M Price Range

$389.4K Average Price

Prior 5 years

About Doug

I am the Broker for Doug Ashley REALTORS, LLC with 30 years of experience. I can be reached at 410-810-0010.

Home Types: House, MultiFamily, Manufactured, Townhouse, Lot/Land, Commercial

Years of Experience: 33

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	8
Total Value	$3,241,500
Average Sale Price	$405,188
Price Range	$50K - $785K

Buyer Deals
Total Deals	3
Total Value	$616,500
Average Sale Price	$205,500
Price Range	$58K - $330K

Seller Deals
Total Deals	16
Total Value	$6,565,400
Average Sale Price	$410,338
Price Range	$50K - $950K

Buyer Deals
Total Deals	3
Total Value	$616,500
Average Sale Price	$205,500
Price Range	$58K - $330K

Seller Deals
Total Deals	48
Total Value	$20,188,417
Average Sale Price	$420,592
Price Range	$50K - $4.3M

Buyer Deals
Total Deals	9
Total Value	$2,007,665
Average Sale Price	$223,074
Price Range	$58K - $363K

5 Year View

Neighborhoods Doug is Experienced In

Chestertown

18 Sales
Kingstown

8 Sales
Greensboro

1 Sale

Doug's Active Listings

$395,000
- 2 Beds
- 1 Bath
- 832 Sq Ft
31673 W Edge Rd

Millington, MD
Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor

Doug Ashley Doug Ashley Realtors, LLC

$649,900
- 4 Beds
- 3.5 Baths
- 2,944 Sq Ft
21163 Chesapeake Ave

Rock Hall, MD
This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split

Doug Ashley Doug Ashley Realtors, LLC

$499,900
- 4 Beds
- 2.5 Baths
- 2,524 Sq Ft
8620 Park Dr

Chestertown, MD
Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot

Doug Ashley Doug Ashley Realtors, LLC

Recently Sold

$278,500

Sold May 14, 2026
- 3 Beds
- 1 Bath
107 Longfellow Dr

Chestertown, MD
- 6% Below List
- 11 Days On Market
- Current Est. Value $300K
Doug Ashley Doug Ashley Realtors, LLC

$355,000

Sold Dec 9, 2025
- 3 Beds
- 3 Baths
- 2,988 Sq Ft
10740 Worton Rd

Worton, MD
- $119/SF
- 58 Days On Market
- Current Est. Value $377K
Doug Ashley Doug Ashley Realtors, LLC

$785,000

Sold Oct 3, 2025
- 3 Beds
- 2 Baths
- 1,841 Sq Ft
201 Dogwood Lodge Ln

Millington, MD
- $426/SF
- 59 Days On Market
- Current Est. Value $816K
Doug Ashley Doug Ashley Realtors, LLC

$50,000

Sold Aug 13, 2025
- 3 Beds
- 1 Bath
- 1,272 Sq Ft
26743 Medders Rd

Still Pond, MD
- $39/SF
- 42 Days On Market
- Current Est. Value $187K
Doug Ashley Doug Ashley Realtors, LLC

$759,000

Sold Jul 1, 2025
- 5 Beds
- 3 Baths
- 3,394 Sq Ft
7988 Aldan Dr

Chestertown, MD
- $224/SF
- 2 Days On Market
- Current Est. Value $795K
Doug Ashley Doug Ashley Realtors, LLC

$237,000

Sold Jun 30, 2025
- 2 Beds
- 2 Baths
- 1,384 Sq Ft
898 Washington Ave

Chestertown, MD
- $171/SF
- 5 Days On Market
- Current Est. Value $260K
Doug Ashley Doug Ashley Realtors, LLC

$312,000

Sold Jun 13, 2025
- 4 Beds
- 2 Baths
- 1,404 Sq Ft
306 Cedar St

Chestertown, MD
- $222/SF
- 55 Days On Market
- Current Est. Value $330K
Doug Ashley Doug Ashley Realtors, LLC

$465,000

Sold Apr 4, 2025
- 3 Beds
- 1 Bath
- 1,602 Sq Ft
203 Bolton Woods Rd

Sudlersville, MD
- $290/SF
- 136 Days On Market
- Current Est. Value $450K
Doug Ashley Doug Ashley Realtors, LLC

$239,000

Sold Nov 25, 2024
- 3 Beds
- 1 Bath
- 1,202 Sq Ft
5 Rolling Rd

Chestertown, MD
- $199/SF
- 7 Days On Market
- Current Est. Value $263K
Doug Ashley Doug Ashley Realtors, LLC

Awards and Designations

NAR - National Association of Realtors
GRI - Graduate REALTOR Institute

Agent License: Maryland 29249

Doug Ashley

(667) 244-8034

Doug Ashley Realtors, LLC

(667) 244-8034

Homes for Sale by City

Doug Ashley

About Doug

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Doug is Experienced In

Doug's Listings and Deals

Doug's Active Listings

Recently Sold

Awards and Designations